Britney Spears Once Made Out With Ben Affleck

Britney Spears says she once made out with Ben Affleck.

The pop icon made the cheeky reveal on Instagram Wednesday (Feb. 7) alongside a photo of her, the actor and famed songwriter Diane Warren at an event in 1999.

“Cool pic of me and Ben Affleck and Diane Warren years ago,” Spears wrote.

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“He’s such an amazing actor. Did I fail to mention I made out with Ben that night? I honestly forgot… damn that’s crazy,” she continued.

“Wish I could tell you guys the story that happened before that!!! Oh dear, I’m just being a gossip girl!!!” the singer added.

See below:

attachment-Screenshot 2024-02-07 at 15-22-19 XILA MARIA RIVER RED (@britneyspears) • Instagram photos and videos


Spears’ latest revelation stokes some longtime rumors that she and Affleck had a flirtation back in the late ’90s and early 2000s.

According to an old tabloid tear, the photo Spears shared is from a party in 1999 to celebrate her sold-out Baby One More Time tour date in Los Angeles.



Affleck would likely have been dating his then-girlfriend Gwyneth Paltrow at the time, though the two were together on and off between 1997 and 2000. They officially split in October 2000.

A New York Daily News article from May 2000 also reported that Affleck “noticed” Spears when she performed her TV special in Hawaii while he was filming his movie Pearl Harbor on Oahu.

“A Spears confidant said the singer has a bit of a crush on the movie star,” the tabloid reported.

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Gallery Credit: Ryan Reichard